Gentleman's Guide to Valentine's Day

A Gentleman’s Guide to Valentine’s Day

Valentine’s Day is right around the corner, and the pressure is on. While it can feel like one big capitalist cliché, chances are your partner will expect and appreciate some recognition for the relationship you share on V-Day (and you deserve some too!).

The Trouble with Valentine’s Day

Roses, classic but unoriginal

Roses, classic but unoriginal

Unfortunately, the Valentine’s Day marketing machine focuses intensely on getting men to spend money to show their partner how much they love them and likewise, sets their partners up with the expectation that the amount of money spent is equivalent to how he feels. It’s not really fair to either side, as a result, Valentine’s Day can be a dreaded holiday that leaves many unhappy and resentful.

Furthermore, why the forced romance? It’s easy to say that you should show your love for your significant other every day as a matter of course, but the truth is that life often gets the better of us. There is value in being reminded to get outside of the daily routine and give romance and your partner a little TLC.

It is often the case that men and women have different expectations for Valentine’s Day. Let’s be honest here, the main conflict is often about romance vs. sex. Both are important, so how can you approach Valentine’s Day like a gentleman? Regardless of where the holiday came from and what it has become, ultimately it should be about finding a way to celebrate your relationship in a way that leaves you both happy at the end of the night. 

Take the Holiday Back

Here are our top tips for an enjoyable Valentine’s Day:

Talk about it. Forget about subtle hints! You can talk about Valentine’s Day with your partner. She may tell you she likes surprises, but if not, an honest conversation about what both of you want is best. 87% of women say they just want to spend time together, and it’s not about the gift. 

Yes, it is about her. At least, that’s what it looks like from the outside. Men feel pressure to deliver a memorable Valentine’s Day for their partners, and many women will feel judged other women on the gestures their significant other makes. It’s a tough situation to navigate, but you certainly won’t win with the “it’s a cliche so why celebrate it at all” argument.

Focus on the romance. You don’t always need romance to have sex, but Valentine’s Day is not that day. Romance needs to be the priority, and if you do that right, the rest will follow. 

It's mutual

Big gestures are risky

Money is not the solution. You can’t buy thoughtfulness. Big ticket purchases and over-the-top gestures can feel empty if the sentiment is not behind them. 



Avoid cliches, unless you know that’s what your partner likes. Don’t hesitate to buy chocolates and roses if that’s what your partner likes! But don’t buy these items as a default – it can appear to lack thought. Ordering flowers for delivery to her office is a nice touch if Valentine’s Day falls on a workday, and she’ll be the envy of her colleagues.

Case in point: Lingerie isn’t a gift for her, it’s for you. A gift is meant for the receiver, not for the giver, so stay clear of lingerie unless she has expressed interest in receiving it from you. Many women consider lingerie a gift men give to themselves that has nothing to do with her, and all to do with sex. In fact, in a 2008 survey, 22% of men surveyed said they were planning to give lingerie for Valentine’s Day and only 2% of women reported wanting it. Yikes! Those numbers are pretty dismal, but there is a way to avoid the most dangerous part of lingerie giving – ask her to pick out something that makes her feel sexy, and if she wants, shop with her.



For those willing to risk buying it themselves, one final tip: if you buy lingerie, do not guess her size. Giving her something much too large or much too small is going to be misconstrued as a statement about her body (however unintentional it may be), which can be a serious mood killer.

Finally, if you want to set the mood without falling into the potentially dangerous lingerie trap, consider gifts like candles, massages, new sheets, or a custom playlist of mood music.

Mood lighting

Mood lighting

Effort matters. You many not have a large budget to splurge out on jewelry, or you may simply not want to participate in the marketing hype. But, that doesn’t mean you can’t make a nice gesture on V-Day. Putting effort into thinking about the day will clearly show, and it will count for a lot. Write a handwritten note, find a romantic poem, or make her breakfast in bed.

If you are not sure what to write in a note, tell her what your favorite romantic moment together was, describe when and why you first knew you were in love, or simply tell her what makes you love her right now. You may say “I love you” every day, but pairing it with a story will make it feel deeper and more special.

Notes are always more sincere when handwritten

Notes are always more sincere when handwritten

If traditional gifts such as flowers and chocolates are your style, a little personalization will go a long way to making it special. Put together a bouquet yourself of her favorite color or variety and she’ll know you put some thought into it.

Dress the Part. You read GG, so chances are looking good is something you like to do. It’s a holiday, so why not take the opportunity to dress up? You’ll feel more confident, and your partner will probably appreciate your effort too. Or, choose the outfit you know your partner likes the best! Here’s my favorite:

My favorite suit in Raphael's collection: Chalk Stripe by Ralph Lauren Purple Label with Fort Belvedere accessories

My favorite suit in Raphael’s collection: Chalk Stripe by Ralph Lauren Purple Label with Fort Belvedere accessories

Focus on each other. This one’s simple. Make your partner the center of your attention when you’re celebrating. Keep your laptop and phone out of sight, the TV off, and turn the romantic music up!

Foolproof Valentine’s Day Ideas

  • Dinner out is a classic, but for the best service, food, and experience, avoid booking on Valentine’s Day. If you’ve eaten out on V-Day before, you know it’s crowded, over priced, the staff are harried and you get hustled in and out as quickly as possible. Tell your partner you want both of you to take your time and enjoy dinner, so you made reservations for another night so you won’t be rushed. And, don’t forget the reservations (make them now!) because nothing kills romance like waiting in a crowded, freezing entryway for an hour. When V-day falls on weekend (like it does in 2016), brunch is a fun, spontaneous alternative.
  • Cook for her, or cook together. Again, this is about spending time doing something together. Not sure what to serve? Epicurious has a list of menus to choose from and Food & Wine has a great page dedicated to it. Or, pull out your favorite or best dish. This Beef Daube has been a make-ahead classic in our house for years.  If you’re not comfortable cooking, there are many subscription meal services out there (Hello Fresh, Plated, Blue Apron) that allow you to buy meals for two that arrive with all the ingredients, a recipe, and clear instructions how to cook them – simple! Even better, they are usually less expensive per person than a restaurant meal.
Romantic getaway

Romantic getaway

  • Get away for a night. No matter where you live, there is probably a romantic Bed and Breakfast within a couple hours drive. Getting away from the house is a perfect way to turn off the daily habits, distractions, and routine that can inhibit romance and true quality time together.
Cooking Class

Cooking Class

  • Find an activity you both like. Ice skate in the local park, go to the theater or take a cooking class or a dance class. Or, use your time to plan something in the future – a weekend getaway, a trip to the next town or destination event that you can share together.

Of course, even if you follow the leads above, it doesn’t hurt to add a thoughtful gift. So take a look at our Valentine’s Day Gift Guides for Her and our V-Day Gift Guide for Men!

What are your plans for V-Day? What have you had success with in the past?



A Gentleman's Guide to Valentine’s Day
Article Name
A Gentleman's Guide to Valentine’s Day
Our guide to navigating Valentine's Day like a gentleman, with tips and activity ideas
Gentleman's Gazette
3 replies
  1. John Hopkins says:

    By putting together the suggestions give above by C. Bell, this is what I did for the best Valentine’s Day to date according to my significant other:
    I was a recent college graduate, jobless and penniless at the time. Despite that, I collect all the last money I had and went grocery shopping to prepare for dinner all of her favorite dishes. Few hours before her arrival from work, I groomed myself, and I dressed up my best (and at the time only!) suit with my best shoes. Simple and original, this was my Valentine’s gift for her: the best of myself!

  2. Robert Miller says:

    I have a Valentines Day tradition that my wife start looking forward to and counting the days right after the first of the year.
    We agree to take the day off, send our Teenage daughter to her sisters and totally enjoy each others company alone for the entire day. I buy nuts, meats, cheeses, chocolates, crackers and Champagne, pull out 3 or 4 of our favorite romantic comedies and we spend the entire day in our pajamas sipping champagne, eating treats, watching movies and thoroughly enjoying each others company.

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